Photo by ViajandoconAna Rustrian

Holiday Rentals in Montgomery

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Montgomery

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (108)
"Awesome "
The price is €262
includes taxes & fees
7 Apr - 8 Apr
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.6 out of 10, Exceptional, (5)
"Plenty of room for my family"
The price is €307
includes taxes & fees
8 Apr - 9 Apr
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

9.6 out of 10, Exceptional, (39)
"A wonderful host with a beautiful & comfortable home. All the necessities, plus more! A must stay at. "
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

High Falls Restorative Cabin in the Woods!

10.0 out of 10, Exceptional, (18)
"We had a great time during our few days in High Falls. The cabin was exactly as pictures, and super clean and well kept! The area is great for hiking and the welcome booklet was really helpful! Would definitely stay here again :)"
High Falls Restorative Cabin in the Woods!

Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

9.8 out of 10, Exceptional, (57)
"Clean and welcoming. Deck is a great attraction. Price point is what attracted me as we were visiting Beacon & couldn’t find a place that didn’t break the bank. Was a little surprised to discover that this is an apartment addition to an existing house; we could hear the family members inside, and I hope we weren’t too noisy for them. Overall cozy and a nice respite. Thank you."
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

10.0 out of 10, Exceptional, (284)
"I visited my college aged son over the weeend for a special event and wanted to stay somewhere with a little something special rather than a hotel. This property exceeded my expectations. Even with winter still lingering, the lake view was spectacular and was highlighted by the home's back wall of windows. Also, Don is a very responsive host and made sure the home had everything you could need - grill, grill tools, pots/pans, appliances, etc. I truly appreciated the hospitality. I hope to stay...
The price is €339
includes taxes & fees
11 Apr - 12 Apr
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

9.8 out of 10, Exceptional, (93)
"We had a wonderful family long weekend at Michele’s beautiful home in the Hudson Valley. We were there to celebrate the birthdays of my husband, son, and grandson. The house was comfortable and well equipped to make meals. Michele the host couldn’t be more responsive. There are many great hikes and wineries close by. This was a 5 star expereince enjoyed by all."
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

Red Barn Retreat - Shawangunk Mountains Getaway

10.0 out of 10, Exceptional, (37)
"Needed rest and quiet away from the city! Not only was this the perfect location, but William is a fantastic host. Great communication before and after, from directions to access and operation with kindness and generosity of spirit. Will return! "
Red Barn Retreat - Shawangunk Mountains Getaway

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

10.0 out of 10, Exceptional, (2)
"My family and I had a fantastic stay! The house was even more beautiful and spacious than we expected, making it the perfect home base for our weekend trip to Mount Peter. It was clean, cozy, and had everything we needed for a comfortable and relaxing stay. My parents live nearby in Warwick and this will definitely be my go-to VRBO recommendation for anyone visiting the area. We can’t wait to come back!"
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Expansive Views; Miles of River & Mountains Walk to Train, Main St, DIA

10.0 out of 10, Exceptional, (1)
"Had a wonderful, relaxing stay here. Convenient location allowed us to walk everywhere we wanted to go!"
Expansive Views; Miles of River & Mountains Walk to Train, Main St, DIA

Cabin in the heart of the Hudson Valley, Cabin 4

9.0 out of 10, Wonderful, (21)
"Exactly as described."
The price is €165
includes taxes & fees
7 Apr - 8 Apr
Cabin in the heart of the Hudson Valley, Cabin 4

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

10.0 out of 10, Exceptional, (48)
"This is an adorable cottage. It is very clean and well appointed. The kids (and adults) really enjoyed the detached game room. The hot tub and fire pit made for very relaxing evenings. We really enjoyed our time here. "
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Mountain View escape

10.0 out of 10, Exceptional, (50)
"We loved everything! Every detail was perfect. It’s beautifully decorated and super clean. Can’t wait to come back! The king bed is super comfy and the shower is amazing! "
Mountain View escape

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Trails Head Cabin

9.8 out of 10, Exceptional, (78)
"Great place to relax near the Delaware Water Gap. Quiet and peaceful. "
The price is €188
includes taxes & fees
7 Apr - 8 Apr
Trails Head Cabin

Catskills mountain gateway house.

9.8 out of 10, Exceptional, (17)
"The house comfortably slept the six of us."
Catskills mountain gateway house.

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2.0 star property
9.0 out of 10, Wonderful, (6)
"This property is great, our stay here was just amazing from start to finish. Communication with the host was great, we left some items there and the host was super accommodating. Would recommend this property very highly."
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

Perfect for families and large groups

9.6 out of 10, Exceptional, (12)
"The property is beautiful and was perfect for our stay. We were in town to see a family members art exhibit. It was my father first stay at a rental property like this and was a good experience for him. We really enjoyed the game room and projecter tv to watch the Superbowl! It was a great place for our family to come together. Thank you!"
Perfect for families and large groups

Waterfront Modern Home with Fast Wifi & Hot Tub

9.8 out of 10, Exceptional, (13)
"Family time, hiking, visiting and touring the area. Views are great - saw a bald eagle on day 1! The home is very comfortable and had everything we needed. The owner has thought out all the details - extra toilet paper to spices! Nicely appointed home. Greenwood Lake is a nice area to relax. "
The price is €437
includes taxes & fees
7 Apr - 8 Apr
Waterfront Modern Home with Fast Wifi & Hot Tub

Lovely 3BR Home with parking-Walk to WP Gate!

10.0 out of 10, Exceptional, (2)
"Close to west point where we were able to attend the sporting event. It is walking distance to the small town outside campus where you can find local shops for eating or shopping. ."
The price is €210
includes taxes & fees
7 Apr - 8 Apr
Lovely 3BR Home with parking-Walk to WP Gate!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Montgomery
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Montgomery you may be interested in

Holiday Inn Express & Suites Montgomery by IHG

2.5 star property
8.8 out of 10, Excellent, (701)
"Everything was great. Friendly staff. Clean and quiet hotel. Breakfast buffet was good and clean. Will stay again."
The price is €105
includes taxes & fees
20 Apr - 21 Apr
Holiday Inn Express & Suites Montgomery by IHG

Super 8 by Wyndham Montgomery Maybrook

2.5 star property
6.4 out of 10, (1003)
"Awesome staff, very welcoming. The woman at the front desk gave me a plastic fork so I could eat my dinner when I arrived. They were also very helpful when I had a last minute itinerary change. Little noisy due to the truck stop being next door but I know that’s out of their control."
The price is €74
includes taxes & fees
27 Apr - 28 Apr
Super 8 by Wyndham Montgomery Maybrook

Borland House Inn

3.0 star property
9.0 out of 10, Wonderful, (107)
"Perfect stay "
The price is €118
includes taxes & fees
7 Apr - 8 Apr
Borland House Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Are there holiday rentals in Montgomery?

Yes, there are holiday rentals in Montgomery close to Orange County Arboretum, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Montgomery has a good selection of restaurants. Make sure you have time to check out the gardens and shopping during your trip.

What are some of the best holiday rentals that Montgomery has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Montgomery offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and an electric kettle, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Montgomery?

Choose from 13 Expedia holiday rentals in Montgomery for a memorable holiday.

What can I see and do in Montgomery?

Orange County Arboretum and Thomas Bull Memorial Park are a couple of lovely local spots to get outside and enjoy nature. You’ll find favourite places to visit such as LEGOLAND® New York and Woodbury Common Premium Outlets in the wider area.

What’s a holiday rental in Montgomery like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montgomery. Holiday rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for small groups.